2,4-Dibromo-6-chloroaniline → HCID 22482744, compound

HRID 2182072Notes

Reaction equation

HRID 2182072 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([Br:9])[CH:5]=[C:4]([Br:10])[CH:3]=1.Br[CH2:12][C:13](=[C:15]([C:18]#[N:19])[C:16]#[N:17])[CH3:14]>C(O)(C)C.O1CCCC1>[NH2:19][C:18]1[N:8]([C:7]2[C:2]([Cl:1])=[CH:3][C:4]([Br:10])=[CH:5][C:6]=2[Br:9])[CH:12]=[C:13]([CH3:14])[C:15]=1[C:16]#[N:17]

Participants

5

Reactant 2

HCID 42959822,4-Dibromo-6-chloroanilineHCID 10921206HCID 10921206, compound

Product 1

HCID 22482744HCID 22482744, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.3 g of 6-chloro-2,4-dibromoaniline and 3.5 g of 2-(2-bromo-1-methylethylidene)malononitrile was dissolved in a mixed solution of 10 ml of isopropanol and 10 ml of tetrahydrofuran. The reaction mixture was heated for 2 hours while being concentrated at 120° C. Water was poured into the reaction mixture. The reaction mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure and was allowed to stand for crystallization to yield 1.9 g of 2-amino-4-methyl-1-(2,4-dibromo-6-chlorophenyl)pyrrole-3-carbonitrile.

Workup

  1. temperatureThe reaction mixture was heated for 2 hours
  2. concentrationwhile being concentrated at 120° C
  3. additionWater was poured into the reaction mixture
  4. extractionThe reaction mixture was extracted with chloroform
  5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationAfter the desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customto stand for crystallization

Sources & evidence

ORD record
ord-3178361a09df47868d2776c702c15811
Source dataset
uspto-grants-2005_05
Patent number
US06894168B2

Reaction notes

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